Search Vacation Homes in Castel San Gimignano

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 958 Vacation Homes in Castel San Gimignano with updated reviews, rates, and availability.

Pool
Independent villa with panoramic garden
9.6 out of 10, Exceptional, (42)
"Das Haus ist gemütlich eingerichtet. Der Ausblick ist atemberaubend schön. Erholung pur. Paolo und Mercina sind sehr hilfsbereit und immer erreichbar. Im Ort gibt es ein tolles Restaurant (La Grotta di Tiburzi), das sehr empfehlenswert ist. Wir hatten leider einige Regentage in unserem 14 tägigen Osterurlaub, wofür natürlich niemand etwas kann. Und wir haben die Entfernungen zu vielen Sehenswürdigkeiten der Toskana total unterschätzt. So sind für die Besichtigungen der wunderschönen Städte...
Independent villa with panoramic garden
Pool
LUXURY COTTAGE IN TUSCAN ESTATE - POOL - NEXT TO A GOLF COURSE! (MORAIOLO)
10.0 out of 10, Exceptional, (30)
"We loved this villa and it's surroundings. If you're looking for a remote getaway, this is a definite winner. The roads leading to the villa are a little sketchy but as long as you have a decent vehicle you will be fine. Great place to stay if you have a car and are wanting to do day trips."
LUXURY COTTAGE IN TUSCAN ESTATE - POOL - NEXT TO A GOLF COURSE! (MORAIOLO)
Pool
detached villa with private pool and garden
9.0 out of 10, Wonderful, (14)
"Superb private villa with enclosed pool & garden only 5 mins walk from the town. Federico is a friendly & helpful host. We were even given fresh eggs by his Dad! Views from the garden are lovely. We had a great stay - thank you. If you are taking a dog just check the costs - we paid £50 when we booked and were charged a further €70 when we left."
detached villa with private pool and garden
Save an average of 15% on thousands of hotels when you're signed in
Holiday Home Exterior [summer]
Belvilla by OYO Il Camino
10.0 out of 10, Exceptional, (1)
"We stayed for a week and this was one of our better holidays."
Belvilla by OYO Il Camino
Property grounds
RAFFAELLO - Firenze /Siena /San Gimignano - SWIMMING POOL AND TENNIS COURT
10.0 out of 10, Exceptional, (6)
"We had a such a wonderful visit. The house is very comfortable and very well equipped. The location is perfect for day trips to many interesting towns and beautiful sights. When not touring the views, pool, and tennis court can make for a relaxing day."
RAFFAELLO - Firenze /Siena /San Gimignano - SWIMMING POOL AND TENNIS COURT
Exterior
Independent house in the hills of the Sienese countryside
10.0 out of 10, Exceptional, (64)
"To begin, this was one the best homes we have had the luck and pleasure to experience. The small house felt like a home. Emanuela, Roberto, and their family were kind, welcoming, and helpful. Their farm and home are a life of love and exacting design and craftsmanship. The necessities are all short drives away; small towns and the larger communes provided learning, great food, history, and art. The stay was relaxing because of the care and attention to detail that the owners supplied in...
Independent house in the hills of the Sienese countryside
Pool
LUXURY COTTAGE IN TUSCAN ESTATE - POOL - NEXT TO A GOLF COURSE! (FRANTOIO)
10.0 out of 10, Exceptional, (37)
"This property was exactly as pictured, clean and beautiful. We had an amazing Tuscan vacation! The location and beauty could not be beat. Thank you!"
LUXURY COTTAGE IN TUSCAN ESTATE - POOL - NEXT TO A GOLF COURSE! (FRANTOIO)
Holiday Home Exterior [summer]
Belvilla by OYO San Francesco Uno
10.0 out of 10, Exceptional, (11)
"Wir hatten als Familie einen super Urlaub 😊 Das Haus und das Anwesen sind traumhaft gelegen eine Ruheoase. Schöner Ausgangspunkt um die Toskana zu entdecken. Riccardo ist ein toller Gastgeber und wir würden sehr gerne wiederkommen. 5 Sterne plus für dieses Anwesen"
Belvilla by OYO San Francesco Uno
Villanovia
Country House & Spa - Inside Nature with panoramic views, Art Surrounded
9.8 out of 10, Exceptional, (47)
"A wonderful house in an outstanding area of natural beauty. Our group had an excellent holiday with the most charming hosts. We will certainly try to repeat the experience."
Country House & Spa - Inside Nature with panoramic views, Art Surrounded
Property grounds
Le Macine, a wonderful ancient restored watermill with Pool
9.6 out of 10, Exceptional, (62)
"We stayed here for 10 nights and thoroughly enjoyed the Villa, the Tuscan ambiance and the close proximity to Volterra. The house manager, Allisandro (Alex) was a great host. Flawless communication, friendliness, attention to our needs and providing local advice were all excellent and appreciated."
Le Macine, a wonderful ancient restored watermill with Pool
Pool
Lovely converted barn with enclosed garden and private pool
9.6 out of 10, Exceptional, (50)
"We had a lovely stay in a converted barn with pool. Very rustic but quiet and close to all the places we wanted to visit. We had a car"
Lovely converted barn with enclosed garden and private pool
Outdoor dining
Luxury villa with fantastic views, pool, 4 bedrooms, 2 bathrooms
9.8 out of 10, Exceptional, (61)
"This villa was perfect for our stay. It is beautiful, super comfortable (we had 9 adults) and private yet only 10 min drive to a grocery store and cute restaurants. And a great location for day trips to Siena and local wineries. The hosts were easy to communicate with, and we loved our in home dinner prepared by Simona. I cannot recommend this place enough."
Luxury villa with fantastic views, pool, 4 bedrooms, 2 bathrooms
Exterior
House in enchanting hill location surrounded by vineyards and olive groves
10.0 out of 10, Exceptional, (31)
"We wanted to stay someplace in quiet beautiful Tuscany and this property was located perfectly. The house is a guest house and the main house is near. It is perfectly and remotely located with the most beautiful views! The patio and outdoors are so beautiful and rustic. It is a drive to do anything but so many little towns and villas to visit. Note, the bedroom is a loft with a sturdy steps but low ceiling."
House in enchanting hill location surrounded by vineyards and olive groves
Exterior
Holiday house with private pool and fenced garden
10.0 out of 10, Exceptional, (41)
"Hosts were very gracious and friendly. Home was clean and well maintained. Property was gorgeous. Host supplied local eateries that were great and where local market was. Highly recommend this home!"
Holiday house with private pool and fenced garden
Pool
House with swimming pool. Medieval village in the heart of Chianti Classico
10.0 out of 10, Exceptional, (102)
"We had wonderful stay at Localita Granaio and in the Castellini in Chianti area. The villa was amazing with its history and setting and we loved the beautiful views as we sat on the patio with our wine and cheese. Our host Pietro could not have been better- helpful but not intrusive, informative and friendly. The general area also had so much to offer. We would go back in a minute! Thanks Pietro"
House with swimming pool. Medieval village in the heart of Chianti Classico
Pool
Holiday Home 'La Loggia di Giulia' with Private Terrace, Whirlpool and Garden
9.8 out of 10, Exceptional, (6)
"Beautiful view"
Holiday Home 'La Loggia di Giulia' with Private Terrace, Whirlpool and Garden
Pool
In the hearth of Chianti, lovely country house
10.0 out of 10, Exceptional, (64)
"Casa splendida, molto più bella di come appare nelle foto, arredata con grande gusto per i dettagli, dotata di tutto, circondata da colline e cipressi, con una veranda all'aperto dove mangiare, rilassarsi e stare insieme ed una piscina non grande ma circondata dal verde e piacevolissima."
In the hearth of Chianti, lovely country house
Pool
Indipendendent house with private garden and swimming pool
10.0 out of 10, Exceptional, (50)
"We hebben een fantastisch fijn verblijf gehad met ons gezin met onze 2 kinderen in leeftijd 8-12 jaar in dit leuke huis. Het panoramisch uitzicht rondom het huis is adembenemend en met recht prachtig. Heel prive, ruim voldoende ruimte binnen en buiten, fijn zwembad en badkamer. Hoewel aan de weg, viel het geluid/overlast heel erg mee. Ontvangst en contact met verhuurder is heel prettig geweest, met hulp ook voor restaurants en tips voor activiteiten. Dank nogmaals hiervoor. En excuses dat we...
Indipendendent house with private garden and swimming pool
Property grounds
Info House
9.8 out of 10, Exceptional, (6)
"Giovanni was an amazing host. He even gave us a welcoming gift of a bottle of wine and apples. I had such an incredible time just relaxing in the peace and quiet and getting some writing done. I would recommend this spot to anyone who is interested in doing the same."
Info House
Outdoor dining
HOUSE WOW panoramic terrace *.*
10.0 out of 10, Exceptional, (15)
"I rarely give a 5 star rating but this property is incredible. When it comes right down to it, people make all the difference. Emanuela was so friendly and accommodating. She was just so happy. She checked on us and helped us with our questions. Beyond that, the apartment is perfect. We so enjoyed our time on the terrace. The building is relatively quiet and we enjoyed watching all the animals living in the apt below us, especially Theo and all the turtles! Highly recommend and we will return....
HOUSE WOW panoramic terrace *.*
Don't see what you're looking for?
See all available properties in Castel San Gimignano
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Castel San Gimignano

Breakfast meal
Il Battistero Siena - Residenza d'Epoca
9.6 out of 10, Exceptional, (117)
"The staff is friendly and helpful, an asset to this hotel. "
The price is AED 598
AED 665 total
includes taxes & fees
5 Jun - 6 Jun
Il Battistero Siena - Residenza d'Epoca
Room
ApartHotel Anghel
8.2 out of 10, Very Good, (276)
"The postive is checkin experiene is easy as the receptionist is very nice. She communicated well. The negative is the room are not insulated. You can hear other rooms closing their doors and kids running in the hallway. "
The price is AED 364
AED 410 total
includes taxes & fees
29 May - 30 May
ApartHotel Anghel
Pool
panoramica casa con piscina privata
7.8 out of 10, Good, (7)
"We spent a very enjoyable week in picturesque Chiusdino. Loved the little town with shops and restaurants (our tip: il minestraio!) within walking distance and great views of the countryside. Went to Siena, Firenze and San Gimignano and walked to the abbey of San Galgano. The house is spacious with 2 big bedrooms and 2 bathrooms and is equipped with plenty of towels. We had the (guilty) pleasure of the pool with a great view and used the outside dining area a lot. Tip: An extra cutting board and...
The price is AED 437
AED 727 total
includes taxes & fees
4 Jun - 5 Jun
panoramica casa con piscina privata
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Recent reviews of Castel San Gimignano hotels
Expedia verified reviews